


In Hindsight

by SergeantPixie



Category: Supernatural, The Vampire Diaries (TV)
Genre: DEAN IS AN EMOTIONAL IDIOT, Elena needs to love herself, F/M, Sorry Not Sorry, Wildest Dreams AU, You're Welcome, here have bittersweet deanlena, why am I allowed to write things
Language: English
Status: Completed
Published: 2015-11-27
Updated: 2015-11-27
Packaged: 2018-05-03 16:08:12
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,759
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5297636
Author URL: https://archiveofourown.org/users/SergeantPixie/pseuds/SergeantPixie
Summary: <blockquote class="userstuff">
              <p>Sometimes it's the things you don't say that you wish you could take back.</p>
            </blockquote>





	In Hindsight

**Author's Note:**

> As some of you might've guessed by the title, it is definitely inspired by Taylor Swift's Wildest Dreams, and there are a couple of references throughout. As for timelines, for TVD it takes place the summer after Elena was sacrificed, so between s2 and s3, and a slightly alternate beginning s3 I guess. It's pre-series for SPN, probably two years before s1.

She was just another girl at the bar. Pretty face, nice legs, an abundance of brown hair, full lips—nothing special. It was her eyes that made Dean take a second look. Well, her legs warranted the second look, but the eyes pulled him back in for a third glance. She had sad eyes.

She was young, the softness of her face told him that much, but her eyes were tired, she had old eyes. She looked like she had lived a hundred lifetimes. She sat alone at the bar, quietly sipping her drink, staring at nothing.

He was halfway through his second drink when a blonde frat boy sidled up to her. Her polite disinterest didn't stop him from wrapping his arm around her shoulder. Dean was across the bar at her side before he'd even really thought it through.

"Sorry I'm late, baby," he said easily, taking the seat on her other side. She looked up at him, long eyelashes fluttering in surprise.

"It's okay, I was expecting you to be," she replied, barely missing a beat. She slid out from under the frat boy's arm, subtly angling her body closer to Dean. She took a delicate sip of her drink.

"You couldn't be on time if your life depended on it," she joked sweetly. Dean clutched his heart, pretending to be wounded. He deliberately ignored the frat boy, far more interested in the girl beside him.

"That cuts me deep, baby," he responded. Her eyes twinkled and he gave her a subtle wink before finally turning his attention to the frat boy.

"Who's your friend, sweetheart?" he asked, inspecting the guy in front of him with obvious disdain. She turned back to look at him, eyes wide with surprise, as if she'd forgotten he was there. She turned back and gave Dean a steely smirk that had to be the sexiest thing he'd ever seen.

"You know, I think he was just leaving," she stage-whispered, something icy in her tone. The frat boy rubbed the back of his neck, mumbled something under his breath and wandered off in defeat. Dean and the girl watched him go. When he was halfway back to his friends—all looking utterly delighted at his defeat—the girl turned back to Dean and snorted delicately into her drink.

She cocked her head to the side and gave him a sly grin.

"So do you usually rescue girls from guys in bars?" she asked, sipping her drink. He smirked.

"Of course, someone's got to do it," he replied with an easy shrug. She raised a skeptical eyebrow.

"Right," she agreed sardonically. "And if the girls are grateful well, that's just wonderful," she continued, smirking at him, "And if the girls are pretty well, that's just a bonus," she added sweetly, and then she leaned in real close until he could smell the flowery scent of her perfume. "All those grateful, pretty girls, and you get to be prince charming," she cooed, giving him a playfully unimpressed look as she pulled away. He laughed in surprise.

She leaned back, surveying him critically as she sipped her drink. It was her second drink, but she was methodical in how she drank it, taking small, measured sips. She wanted it to last.

"I prefer knight-in-not-so-shiny-armor, thank you very much," he retorted. She laughed then, giving him a bright smile. He couldn't resist adding, "It's nice too, you know, when those pretty girls have names." He gave her a meaningful smirk. She cocked her head to the side but leaned in just a little.

"Elena," she replied sweetly.

"Elena?" he repeated, liking the way it rolled off his tongue, looking at her expectantly.

"Elena Gilbert," she elaborated. He nodded, satisfied. "Should I call you Sir Knight?" she asked pointedly. He laughed.

"I'm Dean," he told her. She smiled.

"Dean?" she repeated, using the same tone he had said her name in.

"Winchester. Dean Winchester," he told her, surprising himself when he told her his real last name.

"Dean Winchester," she echoed. "I like it," she decided. He liked the way his name sounded in her sweet, low voice.

She took one last sip of her drink, then put it down on the bar. She leaned in very close, her mouth hovering near his ear.

She spoke softly, but he heard every word. "I bet you like it even better when the pretty girl goes home with you." She moved back just enough to look him in the eye. He blinked, mouth dry.

"How are you real?" he asked her bluntly. She tossed her head back and laughed, baring her throat.

The skin of her throat was marred by a pearly pink bite mark that spoke of untold horrors. Dean's focus sharpened, suddenly serious; he leaned forward running his fingers over the scar.

She flinched barely, looking at him with wide eyes. She hadn't expected him to notice. She eyed him warily.

"Interesting scar," he observed carefully. Her skin was soft as silk, the scar barely discernible beneath his fingertips. "Bet it's got an interesting story to go along with it," he said knowingly.

She gave him a weak smile.

"Oh, you know," she said, "I met a guy…" she trailed off. His hand was still on her throat so he slowly retracted it. His eyes were set intently on her face. "Turned out, he wasn't who I thought he was," she finished with a bittersweet smile. Her sad eyes made sense to him now, she knew more about life than most.

Clearing her throat she finished her drink and then looked at him with her head cocked to the side.

"So you're a hunter," she said bluntly. He blinked, surprised at her intuitive leap. She smirked at his reaction. "I know a thing or two," she replied in response to his unspoken question. "So do you just hunt vampires, or?" she asked. He cleared his throat, still trying to catch up to her.

"I hunt whatever needs to be hunted," he told her. She nodded.

"So you don't just save pretty girls in bars," she said, fluttering those long eyelashes at him. He hadn't forgotten about the scar—and while he did want to know more, he found himself being pulled back into her flirtation.

"Nah, that's just a bonus," he agreed. She smiled, looking up at him through her eyelashes.

"Well all heroes deserve rewards," she told him sweetly. He cocked an eyebrow at her. 

"I'm not a hero," he replied gravely. She scoffed, her eyes bright.

"You're someone's hero," she countered. "You save someone, that usually makes you their hero." He half-nodded, conceding easily.

"What about you? Who's your hero? Who saved you?" He asked. She smiled at him slowly.

"Me, I saved me," she said it simply, quietly. "I'm my hero." He looked at her admiringly. He liked that she claimed herself. She could make all the jokes about prince charming and knights that she wanted, but it was obvious that she was the kind of person who knew how to take care of herself.

"What happened to your vampire?" he asked bluntly. She flashed her teeth at him in a semblance of a smile.

"He's still alive, somewhere," she replied. He frowned.

"That's it, he just let you go?" he questioned doubtfully. She shook her head.

"He thinks I died," she explained, tapping the scar on her neck with her fingernails. "He bit to kill, but by some miracle, I lived."

He raised his glass to that.

"Well then, to saving yourself," he said, finishing his drink. She smiled.

"I never thanked you for saving me earlier," she said, changing the subject again. She put her hand on his cheek, leaned in close, and whispered "thank you," against his mouth before she pressed her lips to his.

She kept the kiss light, barely a press of mouth against mouth before she delicately swiped her tongue along his lower lip and nipped at it lightly. He groaned and she pulled her mouth away from his. She leaned her forehead against his and smirked at him expectantly.

"Elena, you don't need to thank me," he began, wondering why he felt the need to be good for this one girl, but she rolled her eyes at him, pressing her lips to his again, effectively cutting him off. Her mouth was soft and warm, but this time she wasn't soft at all. Instead of the delicate press of her mouth against his it was all teeth and tongue. When she pulled back this time, they were both breathing hard.

"Maybe I just want you take me home," she retorted. Finally getting the message he nodded.

"If you insist," he shot back with a smirk.

"I do," she replied instantly. He stood up and offered her his hand. She took it without hesitation.

* * *

In the morning, it was Elena who tried to make her escape before Dean woke up. He woke up before she made it out the door and had her out of her shorts before she could protest. She came back to bed without much protest anyway.

By the time Dean was done with her the day was half over. She was idly looking for her shorts—behind the dresser by the door—wearing nothing but a thin tank top and her underwear and suddenly Dean realized he didn't want her to go at all.

"What are you doing this summer?" Dean asked before he realized the words were out of his mouth. She looked about college student age; he assumed she was on vacation. She turned back to look at him, cocking an eyebrow.

"Wandering," she said carefully. "Why?" she asked, crawling back into bed with him.

"Spend the summer with me," he replied. It was definitely something he'd never done before—asked a girl to spend any extended period of time with him, but she made him just a little bit crazy. She gave him a disbelieving look.

"What would we do?" she questioned, something like a challenge in her eyes. He slid his fingers into her hair, having developed something of an unhealthy obsession with it the previous night. It was soft and thick and smelled like flowers.

"Well you know my job doesn't exactly have vacation plans, but you could help me," he said carefully. She smiled, her eyes sparkling. She leaned closer.

"Like a partner?" she enquired lightly, looking at him expectantly. He pretended to consider it but then nodded.

"Yeah, exactly like a partner," he agreed.

"I've only ever really faced vampires," she pointed out. He pulled her close and kissed her twice, nipping her lower lip.

"I can teach you," he promised. She gave him a coy smile.

"I am a fast learner," she conceded. He laughed.

"I'll bet you are," he agreed huskily. This time, she kissed him, easing herself back into his lap. He kept one hand firmly planted in her hair, the other roaming her soft curves. When air became necessary she pulled back and tilted her head to the side in challenge.

"Convince me, Winchester" she replied simply. He raised a questioning eyebrow at her. "Convince me it's a good idea to spend the summer with you," she elaborated, her words laced with suggestion. He laughed.

"You are insatiable, Gilbert" he accused with an affectionate laugh. She nodded in agreement.

"I absolutely am," she said easily. "Think you can keep up?" she asked challengingly. He pulled her back in for another kiss in response.

Later, her head on his chest, his fingers in her hair, she murmured something against his chest.

"What was that?" he asked, smirking. She huffed.

"I'll stay," she said simply. He grinned, pulling her up until she was nose to nose with him.

"So I convinced you," he teased. She smiled and rolled her eyes.

"You convinced me," she agreed, pressing a soft kiss to his cheek. He ghosted his fingertips up her sides and she giggled against his skin, squirming out of his reach. She giggled again and then gave him a contemplative look.

"You haven't even known me for a full day and you ask me to spend the summer with you?" she questioned. He shrugged, unsure of how to articulate what he was feeling.

"I like being around you," he said it simply, before adding in a conspiratorial undertone, "You make me just a little bit crazy."

She tossed her head back and laughed outright. His fingers came up to trace her scar again. The look she gave him was soft and warm. She pressed a kiss to his palm.

"I like being around you too," she confided softly. He smiled at that.

* * *

 She wasn't lying about being a quick learner. She picked up many of the hunting skills quicker than he'd thought possible. She was a quick study really, eager to learn and full of determination to succeed. She made a good partner.

She was familiar to an extent with many of the weapons they used; she was proficient with a crossbow and handled the kickback on a shotgun like a champ, but it was the handgun where she shined.

The first time Dean handed it over, she had it disassembled and reassembled before he could even point out where the safety was. She turned expectant eyes on him, her mouth curved up teasingly. At the sight of his dropped jaw she shrugged modestly.

"The sheriff's daughter was also my best friend," she said by way of explanation. "I picked up a thing or two." He snorted.

"I can see that," he replied with dry amusement. She smiled cheekily at him.

She was fast and flexible and ended up on top more often than not in their sparring—not that Dean ever minded. Her endurance and pain tolerance were staggeringly high and she had great coordination. It all added up to two options—cheerleader or dancer. Unfortunately, no matter how much he begged and prodded she refused to tell him which of the two it was.

She was good at the research aspect, although Dean could tell it wasn't her favorite. She could do the legwork, but when it came down to it, her best attribute was in her powers of empathy.

Dean was good at getting confessions out of people, his dad was pretty good at it too, and Sam had always been good at saying the soft, sensitive thing that made people cave and tell him more than most. But Elena made people _want_ to tell her things. She said all the right things at all the right times and in return people poured their hearts out to her. She listened and comforted them and made connections in a way Dean had never been capable of.

She was a great hunter; she had only one real flaw. While she would never put anyone else in harm's way—especially not Dean himself—she easily and continuously threw herself in its path with little regard for her personal safety. She took risks with her safety—with her life—that should not pay off as often as it did.

It was the only thing they fought about. Dean thought she had some kind of a death wish. Elena thought it was more important to protect other people than to protect herself. Dean understood to an extent—except that he never wanted anything bad to happen to her. She wasn't the kind of person who put herself before others, and in a way, Dean thought that her agreeing to spend the summer with him was one of the few things she'd done just for herself.

The first week and a half her phone never stopped ringing. If it wasn't phone calls, it was text messages. Damon called the most, but Caroline texted even more. Bonnie left the most voicemails. Tyler sent a text message every day around noon. Ric called every evening at six. Jeremy was the only who ever received a response, and it was only ever a text message. Dean knew their names, but he never asked about any of them, he was afraid that if he asked she would realize that she missed them and leave.

When she left her phone charger in the third motel, Dean tried not to let her see his relief. Her phone died and she never bothered to buy a new charger.

She offered very little information about her life, and Dean offered even less. He knew nothing about her parents, her childhood.

He told her about Sammy once, he mentioned him in passing, and only then had she volunteered that she had a little brother too—Jeremy. He didn't mention his father—or his mother.

He especially didn't talk about the phone calls where his father grew increasingly more frustrated with him. They were supposed to meet back up only a week after he'd met Elena, but Dean kept putting it off. He had a feeling his dad wouldn't approve of his relationship with her, but he also couldn't bring himself to give her up. His father knew something was up, perhaps he even suspected that it was a girl, but Dean stayed tight-lipped about it. The longer he got to keep her, the better.

Even if they didn't share their pasts, Dean found that he knew her better than anyone. She slept less than he did and loved red velvet cupcakes more than any other dessert. She knew all the words to the songs on the radio and could charm the sourest old man even on a bad day. She had the most ridiculous laugh he'd ever heard and could drink most grown men under the table. She was awful at pool and hated pickles.

She knew him just as well. Knew all his favorite songs and his undying love for every kind of pie—especially apple. She could read his mood with a single glance and never complained about his unreasonable addiction to soap operas. She never questioned why he wore the same necklace every day. She knew how to quiet his nightmares by tucking her face into his neck and running her fingers through the hair at the nape of his neck. She was more than just some girl—she was his best friend.

Sometimes he woke up in the middle of the night, her head on his chest, legs tangled up with his, and this feeling would swell in his chest. He couldn't quite name it, but he had his suspicions. It went unsaid, but sometimes he'd catch her looking at him while he was driving and he was sure she felt it too.

They were a great team and it was a perfect summer, but nothing lasts forever. Midway through August, Elena began to retreat even deeper into herself. She didn't even bother trying to sleep at all, often she sat up, arms wrapped around her legs, staring out the motel windows until Dean coaxed her into bed with him. Even there, in his arms, she seemed farther and farther away.

Finally, when they split up to dig up dirt for one case, she came back with a bag from the electronic store. It was a phone charger. She didn't use it right away. Instead, she told him what she'd discovered from the chatty librarian in the tiny library a block from the beach. They finished the case in a matter of days.

Their last night in the tiny beach town, Dean woke just before dawn to find Elena gone. Following a hunch, he walked the three blocks to the beach and found her there. The beach was empty, the sky blue-gray. Tiny fissures of pink and gold streaked the sky, the sun a thin sliver on the ocean. Elena stood at the edge of the water, watching the sun's ascension, her arms crossed over her chest, and cheeks bright with color from the brisk wind.

It was the first time he almost let himself think that word—love. The only thing that suppressed that thought was that summer was nearing its end, and he didn't know how to ask her to stay with him.

She turned, aware of the eyes on her. She smiled at him, her eyes sad and weary again. He smiled back weakly, walking closer. When she stepped into his arms, he held her as tightly against him as he possibly could.

The next day, she charged her phone for the first time since the beginning of the summer.

* * *

 Two days later, she finally used it. He awoke early to find her seemingly gone, but upon closer inspection realized she was in the bathroom. He heard the low murmur of her voice, and a quick glance at the bedside table confirmed his suspicions, her phone was gone. Her voice was too low for him to make out the words, but her tone was serious. When she emerged from the bathroom, her phone was clutched firmly in her hand and her hair was still messy from what little sleep she'd gotten.

Silently she put her phone down and crawled back into bed with him. Without a word he opened his arms and she tucked herself in against his side, all but molding herself to his skin. Pressing her face to his chest, she breathed in the scent of his skin, a smell that had grown comforting and familiar to her far too quickly.

He wrapped his arms around her, one hand tucked into the waistband of her shorts and the other tangled in the length of her hair. Absentmindedly he pressed a kiss to the side of her head, his heart in his throat. He could feel it beating against his Adam's apple as he waited for her to speak, dreading what he knew was coming.

"I have to go home," she murmured at last. His grip tightened imperceptibly. His fingers twisted in her hair, fist clenching. If it hurt her, it didn't show. She didn't even flinch.

"When?" he asked hoarsely. She tucked herself in against him closer, as if she was trying to melt into his skin.

"The end of the week," she replied, her voice tight. He nodded, his fingers loosening their grip on her hair.

"Okay," he agreed, something raging in his chest. He knew he should fight it, should ask her to stay, but he couldn't find the words. He didn't know if it would change anything at all. He didn't know if she would stay.

They laid there for a long time, not speaking, entwined and miles apart.

* * *

 At the end of the week, she directed him back to the bar they'd met at, barely speaking except to give directions. She held his hand the whole way. He didn't have the heart to take it back, so he let her.

When he pulled into the parking lot it was almost noon. There were barely any other cars there, but one stood out—a pale blue Camaro with a black-haired man leaned against it. At the sight of the Impala, the man stood up straight, his gaze fixed on the passenger's seat. Elena's grip tightened to the point of pain but Dean didn't flinch.

Knowing it was time for goodbye didn't make it any easier to speak, so for several long moments they sat in tense silence. Just when the black-haired man seemed to be at the end of his patience, Elena leaned forward and flicked on the car radio.

She turned to Dean, pressing her hand to his cheek like she had done that very first night they'd met at the bar in front of them. Confused, Dean looked into her eyes, and was surprised to see something akin to desperation in them. Elena leaned in, pressing her mouth to his ear urgently.

"Promise me, Dean," she began desperately but then stopped. She cleared her throat, her voice raw. "Promise me you'll remember me," she requested. Dean frowned, pulling back just enough to look her in the eyes. She kept her fingers on his cheek, her dark eyes pleading.

"Like I could forget you," he scoffed, trying to make light of it. She smiled sadly.

"Is that a promise?" she whispered sweetly. He laughed, his voice catching in his throat.

"Damn right, Gilbert," he told her hoarsely. She smiled at him, tears glistening in her eyes, and there, under the scrutiny of the black-haired man, she kissed him one last time.

"Goodbye, Winchester," she whispered against his mouth, and then she peeled her hand from his and she grabbed her bag, slipping out of the car before he could say another word. Before he could ask her to stay.

She was halfway across the parking lot when she turned back. She looked at him, raised her hand in goodbye, and then continued on with determined strides toward the black-haired man.

He opened the passenger door for her, and she glanced back at Dean one more time before she slid into the car. The man closed the door, looked back at Dean with an inscrutable expression, and then slid into the driver's seat.

Dean didn't leave the parking lot for a long time, even after they drove away.

* * *

 Dean didn't tell Sam about Elena, but he found out about her anyway. He brought her up during a stakeout, so suddenly and out of the blue that Dean had to wonder how long he'd wanted to ask about her.

"Dad said there was a girl, once," Sam said. Dean looked over at him, his eyebrow raised, no other expression on his face. "He said you spent a whole summer with her." Dean didn't reply.

"A whole summer with one girl?" Sam gave him a speculating look, like he was hoping Dean would offer more. Dean just looked at him. "What was her name?" Sam asked finally, impatient with his brother's non-reaction.

"Elena," Dean responded at last. Sam blinked.

"What happened with her?" Sam questioned carefully. Dean gave a half-shrug, uncomfortable with the topic. He preferred to think of her as little as possible, he liked talking about her even less.

"She left," he told him simply. Sam gave him a searching look.

"Why?" Sam asked bluntly. Dean rubbed the back of his neck in discomfort.

"She had to go home," he replied shortly. Sam frowned at that.

"Maybe she wanted you to ask her to stay," Sam suggested. Dean nodded.

"Yeah, that's what I thought," he agreed. "But looking back, I realized she wouldn't have stayed even if I'd asked."

"How would you know? You never asked," Sam pointed out. Dean shook his head. He knew Elena better than anyone.

"She's not that kind of girl," he explained. Sam gave him a puzzled look.

"What kind of girl is that?" he enquired. Dean shrugged.

"Not the kind of girl she is," he replied cryptically. He didn't know how to explain it, and frankly he didn't want to. Recognizing a shutdown when he saw it, Sam tried a different tactic.

"What was she like?" Dean sighed heavily, already tired of his brother's questions. Silently he cursed their dad for feeling the need to share such a thing with Sam. He preferred when they weren't talking.

"She was…" Dean trailed off. He shrugged almost helplessly, searching for a good way to explain her. "She was strong," he finally settled on.

"She was strong and brave and she had the saddest eyes I'd ever seen."

Sam didn't reply.

The silence stretched between them long enough that Dean thought the topic had been dropped. But Sam couldn't seem to drop it.

"Maybe you should've asked her to stay, anyway," he began, fixated on the idea of Dean and this girl. "Maybe the only way she would've let herself be the kind of girl that stayed was if you asked her to be." Dean rolled his eyes.

"But I didn't ask, Sammy," he pointed out harshly. "It's a bit too late for that, and hindsight's a useless bitch." Sam blinked at his harsh words.

"It's over, Sammy, just let it go," Dean ordered flatly.

"You first," Sam retorted. Dean didn't have an answer to that.

"She wouldn't have stayed," he repeated stubbornly.

"Sure she wouldn't have," Sam agreed pityingly. It was strange to think that his big brother had any regrets, but here it was, clear as day. Dean had loved Elena, and he'd been too afraid to ask her to stay, so she left.

"Maybe you'll see her again," Sam said hopefully. Dean snorted.

"Sure," he agreed. "In my wildest dreams."


End file.
